The broad objective of this proposal is to develop a practical chiral hydrogen transfer agent which can be used to accomplish the reduction of a wide spectrum of achiral carbonyl compounds to chiral carbinols with high stereoselectivity (hopefully better than 90%). If this can be accomplished, a reagent would then be available for preparing optically active secondary carbinols (and 1-deuterio-primary carbinols) in high enantiomeric purity without resorting to resolution. The same reagent should be able to reduce imines, oximes, lactames, and related nitrogen analogs to chiral amines. Several reagents are contemplated. Two types can be represented by the following structures: NaAl(OCHRCHROCH3) 2H2 and NaAl(OCHRCHRNMe2)2H2. These are analogous to the achiral sodium bis(2- methoxyethoxy) aluminum hydride reducing agent. A systematic investigation of the possible chiral glycols and carbinolamine analogs of this proven achiral reagent will be investigated.